5-Acetyl-1,2-oxazole-3-carboxylic acid → HCID 52920063, compound

HRID 872730Notes

Reaction equation

HRID 872730 reaction equation
[NH2:1][CH2:2][C@@H:3]([N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[C:16]([F:18])[C:13]([C:14]#[N:15])=[C:12]([Cl:19])[CH:11]=2)=[N:6]1)[CH3:4].[C:20]([C:23]1[O:27][N:26]=[C:25]([C:28](O)=[O:29])[CH:24]=1)(=[O:22])[CH3:21]>>[C:20]([C:23]1[O:27][N:26]=[C:25]([C:28]([NH:1][CH2:2][C@@H:3]([N:5]2[CH:9]=[CH:8][C:7]([C:10]3[CH:17]=[C:16]([F:18])[C:13]([C:14]#[N:15])=[C:12]([Cl:19])[CH:11]=3)=[N:6]2)[CH3:4])=[O:29])[CH:24]=1)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 178675215-Acetyl-1,2-oxazole-3-carboxylic acidHCID 67171415(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 52920063HCID 52920063, compoundYield 19.6%

Procedure

(S)-5-acetyl-N-(2-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)-propyl)isoxazole-3-carboxamide was prepared using the method of Example 34(d) starting from (S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (500 mg, 1.794 mmol) and 5-acetylisoxazole-3-carboxylic acid (417 mg, 2.69 mmol). The product was purified twice by Flash-chromatography (normal phase and reverse phase). Yield 19.6%. 1H-NMR (400 MHz; DMSO): δ 1.51 (d, 3H), 2.57 (s, 3H), 3.56-3.77 (m, 2H), 4.65-4.77 (m, 1H), 7.01 (d, 1H), 7.56 (s, 1H), 7.89 (dd, 1H), 7.91 (d, 1H), 7.98 (s, 1H), 9.03 (t, 1H).

Workup

  1. customThe product was purified twice by Flash-chromatography (normal phase and reverse phase)

Sources & evidence

ORD record
ord-a6883b6867184bb788b08e6817da93a2
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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